1. Field of the Invention
The invention is a process for the production of vicinally diacyloxy-substituted compounds including diacyloxyalkanes and esters of diacyloxy fatty acids with alkanols and diacyloxy fatty alcohols and of esters of fatty acids with diacyloxy fatty alcohols which correspond to formulae Ia, Ib, Ic and Id below: EQU R.sup.1 [vic. (O--CO--R.sup.2).sub.2 ]--H (Ia) EQU R.sup.3 [vic. (O--CO--R.sup.2).sub.2 ]--CO--OR.sup.4 (Ib) EQU R.sup.3 [vic. (O--CO--R.sup.2).sub.2 ]--CO--OR.sup.5 [vic. (O--CO--R.sup.2).sub.2 ] (Ic) EQU R.sup.6 --CO--OR.sup.5 [vic. (O--CO--R.sup.2).sub.2 ] (Id)
in which
R.sup.1 is a trivalent saturated C.sub.6-22 hydrocarbon radical, PA0 R.sup.2 is a C.sub.1-3 alkyl radical, PA0 R.sup.3 is a trivalent saturated C.sub.10-21 hydrocarbon radical, PA0 R.sup.4 is a C.sub.1-22 alkyl radical, PA0 R.sup.5 is a trivalent saturated C.sub.16-22 hydrocarbon radical and PA0 R.sup.6 is a C.sub.1-21 alkyl radical. PA0 R.sup.7 (EpO) is an epoxidized C.sub.6-22 alkenyl radical, PA0 R.sup.8 (EpO) is an epoxidized C.sub.10-21 alkenyl radical and PA0 R.sup.9 (EpO) is an epoxidized C.sub.16-22 alkenyl radical PA0 R.sup.1 is a trivalent saturated C.sub.6-22 hydrocarbon radical, PA0 R.sup.2 is a C.sub.1-3 alkyl radical, PA0 R.sup.3 is a trivalent saturated C.sub.10-21 hydrocarbon radical, PA0 R.sup.4 is a C.sub.1-22 alkyl radical, PA0 R.sup.5 is a trivalent saturated C.sub.16-22 hydrocarbon radical and PA0 R.sup.6 is a C.sub.1-21 alkyl radical.
2. Statement of Related Art
Vicinally diacyloxy-substituted compounds are known. Vicinal diacyloxy fatty acid esters have been used inter alia as plasticizers (J. Chem. Eng. Data 5, 231 (1960), as synthetic lubricants (Ind. Eng. Chem. 46, 2205 (1954)) and in foam-regulated cleaning preparations, laundry detergents and dishwashing detergents (DE-C 24 27 125).
There are various known processes for the production of diacyloxy fatty acid esters. For example, vicinal diols may be acylated with the anhydrides of carboxylic acids and/or with carboxylic acid halides, c. Ind. Eng. Chem. 46. The secondary products of the ring opening of epoxides with carboxylic acids, i.e. the (2-hydroxyalkyl)-esters, may also be acylated with anhydrides and/or acid halides, cf. De-C 24 27 125 as cited above and J. Chem. Soc. Perkin Trans. I. 1975, 231 to 241. In addition, vicinal diacyl compounds may be directly produced from the corresponding olefins by oxidative acetylation using Pb(IV) acetate, Tl(III) acetate, Hg(II) acetate, Fe(II) persulfate/acetic acid and Pd(II) acetate. Liebigs Ann. Chem. 138, 297 (1866) reports on the production of vicinal diacetates by reaction of epichlorohydrin with acetic anhydride in a closed loop at 180.degree. C.